Serena Williams' Best Vanity Fair Oscar Party Outfits

Yes, Serena Williams is one of the most famous athletes in the world, but she's also a fashion icon. In fact, her style is just as professional as her tennis skills, as Williams studied fashion. "I have been doing fashion since 2000 — that's when I went to fashion school — so I've been doing this a really long time, more than people actually realize," Williams revealed to Teen Vogue in 2020. As someone who knows a lot about it, it's clear that Williams takes her red-carpet fashion very seriously.

Knowing that, it's unsurprising that she's served so many stunning Vanity Fair Oscar Party looks over the years. In fact, picking our favorites wasn't easy, as the former professional tennis player has been one of the party's most-frequent attendees. Nevertheless, we've made our choices, and in no particular order, here are Williams' best Vanity Fair Oscar Party outfits from the early 2010s to now.

In 2011, Serena Williams attended the event in a beautiful coral gown by Ines Di Santo, which was perfect for saying goodbye to winter. Speaking to People in 2016, Williams' stylist, Kesha McLeod, revealed that this was the first time she worked with Williams for the Vanity Fair Oscar Party. "Under that dress she is wearing flats and a boot, because she had surgery on her toe," the stylist revealed. "It's mesh tulle that was underneath to keep it open for her boot." Because the dress was elegant and simple, Williams was able to go heavy with accessories, opting for gold bangles and a choker necklace.

Yellow isn't a color we see too often at red-carpet events, but Serena Williams definitely made us wonder why that's the case in 2012 when she showed up to the Vanity Fair Oscar Party in a beautiful, backless mermaid gown by Christiane King. The design was the perfect mix of glamorous and fun, ensuring the tennis player's curves were hugged in all the right places. Williams kept the rest of her look simple by adding retro statement earrings and styling her hair in a low updo.

In 2014, Serena Williams gave us perhaps one of her strongest Vanity Fair Oscar Party fashion moments ever. The tennis pro walked the red carpet in a Michael Costello gown that combined floral embellishments with sheer fabric, resulting in a revealing yet sophisticated fashion moment. With her hair in a deep side part and styled in cascading curls, the result was an effortless look that exuded glamour and fun at the same time.

In 2015, Serena Williams seemingly drew inspiration from the dancing-woman emoji for the Vanity Fair Oscar Party that year— you know the one — and the result couldn't have been better. The tennis star rocked an Ines Di Santo design that had a spotlight-stealing thigh-high slit, not to mention that fiery shades like this look incredible on the athlete. "Little do people know, we will do a heel for the red carpet and change into a flat right after," stylist Kesha McLeod told People. "Some women need heels to feel confident. She doesn't." The star paired the look with her signature statement earrings and a classic updo.

Serena Williams always looks stunning in white gowns, and the custom Galia Lahav dress she wore to the 2016 Vanity Fair Oscar Party was no different. Made out of white lace, the gown gave the illusion of a two-piece thanks to the sheer mesh around the waistline. "The flesh tone in the mesh had to look naked, so that was a very scary moment up until the last hour," stylist Kesha McLeod revealed to People at the time. "With the perfection of the fit and having an awesome tailor out in LA, it was one of my favorite moments on her." The plunging neckline helped add the perfect amount of sultriness, and Williams paired the dress with decadent earrings and a sleek lob haircut for that perfect in-between length.

To the 2019 Vanity Fair Oscar Party, Serena Williams wore a custom black-and-blue Armani Privé gown that featured sheer sleeves, a tulle mermaid skirt, and blue sequin flowers all over the bodice. The look was intricate and maximalist, and while it could have easily leaned into too-busy territory, Williams knew that slicked-back hairstyles are perfect for any occasion. That and her statement earrings were all the gown needed.

While many of the celebrities who attend the Vanity Fair Oscar Party reach for glamorous, floor-length gowns, every now and then, we see a shorter hemline. And as a veteran of the event, Serena Williams had some fun with her look by wearing a shorter silver Versace dress and a blond Italian bob in 2022. Interestingly, Williams revealed that the dress was one she had already worn. "So the night before, I called Donatella [Versace] and I'm like, 'I don't know what to do, my dress doesn't fit. I have nothing to wear to Vanity Fair,'" she told Vogue that year. "She's like, 'What if we take that dress we made for Critics Choice, cut it, and just make a fresh dress?'" The dress and Williams were ultimately both of a breath of fresh air. 

In 2025, Serena Williams opted out of fashion risks by wearing a classic, strapless Dolce & Gabbana dress in black. Of course, that didn't mean the look was boring — the bodice was covered in sequins, and the skirt was sheer with a thigh-high slit reminiscent of Angelina Jolie's infamous 2012 Academy Awards gown. The look was styled by Dion Demetries, and with Williams' voluminous blond locks and eye-catching jewelry, it definitely ended up being one of the night's winners.

Now, if you haven't had enough Academy Awards fashion, check out the worst-dressed celebs in Oscars history.